314730-65-9

Basic information

• Product Name: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine
• Synonyms: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine
• CAS NO: 314730-65-9
• Molecular Formula: C₂₆H₃₈ClN₂P
• Molecular Weight: 445.02
• Product Categories: Catalysis and Inorganic Chemistry;Phosphine Ligands;Phosphorus Compounds
• Mol File: 314730-65-9.mol
• Article Data: 7

Chemical Properties

• Melting Point: 212-220 °C
• Appearance: /
• CAS DataBase Reference: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine(314730-65-9)
• EPA Substance Registry System: 2-Chloro-1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine(314730-65-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 314730-65-9(Hazardous Substances Data)

Upstream product

• 14694-95-2 Wilkinson's catalyst 
• 314730-71-7 ((C₃H₇)2C₆H₃)2N₂C₂H₄P⁽¹⁺⁾*CF₃SO₃^(1-)=((C₃H₇)2C₆H₃)2N₂C₂H₄PCF₃SO₃ 
• 1406696-26-1 1,1 ,3,3-tetradiisopropylphenyl-2,2-bi-1,3,2-diazaphospholidine 
• 24544-04-5 2,6-diisopropylbenzenamine 
• 134030-22-1 N,N'-bis(2,6-diisopropylphenyl)ethane-1,2-diamine 

Downstream Products

• 314730-71-7 ((C₃H₇)2C₆H₃)2N₂C₂H₄P⁽¹⁺⁾*CF₃SO₃^(1-)=((C₃H₇)2C₆H₃)2N₂C₂H₄PCF₃SO₃ 
• 1330191-24-6 1,3-bis(2,6-diisopropylphenyl)-2-(diphenylphosphanyl)-1,3,2-diazaphospholidine 
• 1365996-68-4 lithium (2-[1,3-di-(2,6-diisopropyl)phenyl]-1,3,2-diazaphospholidin-2-yl)benzenesulfonate 
• 1428904-93-1 1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine 
• 1428904-95-3 1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine-borane 
• 1428904-94-2 C₃₀H₅₀AlN₂OP 
• 854929-36-5 1,3-bis(2,6-diisopropylphenyl)-1,3,2-diazaphospholidine-2-oxide 
• 1406696-26-1 1,1 ,3,3-tetradiisopropylphenyl-2,2-bi-1,3,2-diazaphospholidine 

Relevant articles and documents

Amine-Catalyzed Phospha-Michael Reaction of α,β-Unsaturated Aldehydes and Ketones with Multifunctional N-Heterocyclic Phosphine-Thioureas as Phosphonylation Reagent

An efficient amine-catalyzed phospha-Michael addition reaction of α,β-unsaturated aldehydes/ketones with N-heterocyclic phosphines for the synthesis of ?-ketodiazaphosphonates has been developed. With freedom from nucleophile additives, this mild process affords a range of structurally diverse ?-ketodiazaphosphonates in moderate to excellent yields. Importantly, various α,β-unsaturated ketones were also tolerated in this process and gave moderate yields.

Controlled acrylate insertion regioselectivity in diazaphospholidine- sulfonato palladium(II) complexes

Diazaphospholidine-sulfonato Pd(II) complexes [{κ2-P,O-(N- Ar2C2H4N2P)C6H 4SO3}PdMe(L)] 1-L (L = dmso, pyridine, lutidine, or μ-LiCl(solvent); 1a: Ar = Ph, 1b: Ar = 2-MeC6H4, 1c: Ar = 2-MeOC6H4, 1d: Ar = 2,4,6-Me3C 6H2, 1e: Ar = 2,6-iPr2C6H 3, 1f: Ar = 2,6-(p-tolyl)2C6H3) were prepared and structurally characterized. The regioselectivity of methyl acrylate (MA) insertion into the Pd-Me bond is entirely inverted from >93% 1,2-insertion for bulky substituents (1d-f, yielding the insertion products [(PO)Pd{κ2-C,O-CH2CHMeC(O)OMe], 12) to the usual electronically controlled 2,1-insertion (>95%) for the less bulky Ar = Ph (1a, yielding the insertion product [(PO)Pd{κ2-C,O- CHEtC(O)OMe], 11, and β-H elimination product methyl crotonate). DFT studies underline that this is due to a more favorable insertion transition state (2,1- favored by 12 kJ mol-1 over 1,2- for 1a) vs destabilization of the 2,1-insertion transition state in 1d,e. By contrast, MA insertion into the novel isolated and structurally characterized hydride and deuteride complexes [{κ2-P,O-(N-Ar2C 2H4N2P)C6H4SO 3}PdR(lutidine)] (Ar = 2,6-iPr2C6H3; 9e: R = H, 10e: R = D) occurs 2,1-selectively. This is due to the insertion occurring from the isomer with the P-donor and the olefin in trans arrangement, rather than the insertion into the alkyl from the cis isomer in which the olefin is in proximity to the bulky diazaphospholidine. 1a-f are precursors to active catalysts for ethylene polymerization to highly linear polyethylene with M n up to 35 000 g mol-1. In copolymerization experiments, norbornene was incorporated in up to 6.1 mol % into the polyethylene backbone.

N-Heterocyclic phosphenium cations: Syntheses and cycloaddition reactions

A series of trifluoromethanesulfonate (OTf) salts of N-heterocyclic phospheniums (NHP) bearing phenyl (1a), para-methoxyphenyl (1b), 2,6-diisopropylphenyl (1c) and mesityl (1d) substituents is reported. The compounds 1b-d are made by a modification to a literature procedure that improves the overall yields for 1c and 1d by 15 and 23%, respectively. Two unwanted side-products in the synthesis of 1d, the diammonium salt, [(2,6-iPr-C6H3)N(H)2CH2CH 2N(H)2(2,6-iPr-C6H3)]Cl2 (4) and the bisphosphine (2,6-iPr-C6H3)N(PCl 2)CH2CH2N(PCl2)(2,6-iPr-C 6H3) (5), are crystallographically characterized, as is the intermediate cyclic chlorophosphine, C1PN(4-OMe-C6H 4)CH2CH2N(4-OMe-C6H4) (3b). The phenyl-substituted NHP 1a is fully characterized, including by X-ray crystallography, for the first time; this compound contains a short P-O contact of 2.1850(14) A Cycloaddition reactions of 1a-d with 2,3-dimethyl-1,3- butadiene give the expected spirocyclic phospholeniums, 7,8-dimethyl-1,4-diaryl- 1,4-diaza-5-phopshoniaspiro[4.4]non-7-ene, as their OTf salts (6a-d), while reactions with N,N′-dimesityl-1,4-diaza-1,3-butadiene give, except in the case of 1c, which is too bulky to react, the aza analogues, 1,4-dimesityl-6,9- diaryl-1,4,6,9-tetraaza-5-phosphoniaspiro[4.4]non-2-ene (7a, 7b and 7d). The sterically congested 7d is in thermal equilibrium with 1d and free diazadiene, and undergoes a substitution reaction with 2,3-dimethyl-1,3-butadiene to give 6d.